CA1069825A - Compositions and method of treating hypertension - Google Patents

Compositions and method of treating hypertension

Info

Publication number: CA1069825A
Authority: CA; Canada
Prior art keywords: compound; alpha; dihydroxyphenyl; hydrazino; propionic acid
Prior art date: 1975-08-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA258,527A

Other languages

English (en)

French (fr)

Inventor

Alexander Scriabine

Clement A. Stone

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Merck and Co Inc

Original Assignee

Merck and Co Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-08-13

Filing date

1976-08-05

Publication date

1980-01-15

1976-08-05 Application filed by Merck and Co Inc filed Critical Merck and Co Inc

1980-01-15 Application granted granted Critical

1980-01-15 Publication of CA1069825A publication Critical patent/CA1069825A/en

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title abstract description 16
206010020772 Hypertension Diseases 0.000 title abstract description 5
238000000034 method Methods 0.000 title abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 10
231100000252 nontoxic Toxicity 0.000 claims abstract description 8
230000003000 nontoxic effect Effects 0.000 claims abstract description 8
241000555028 Sternidius alpha Species 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 39
-1 2-acetamidoethyl Chemical group 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 4
CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 claims 2
150000002148 esters Chemical class 0.000 abstract description 2
230000036772 blood pressure Effects 0.000 description 12
230000000694 effects Effects 0.000 description 9
241001465754 Metazoa Species 0.000 description 7
239000002775 capsule Substances 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
239000000463 material Substances 0.000 description 6
QNAYBMKLOCPYGJ-UHFFFAOYSA-M alaninate Chemical compound CC(N)C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-M 0.000 description 5
239000006187 pill Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
239000011149 active material Substances 0.000 description 3
230000004872 arterial blood pressure Effects 0.000 description 3
NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 3
239000003814 drug Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
238000007912 intraperitoneal administration Methods 0.000 description 3
235000019260 propionic acid Nutrition 0.000 description 3
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
239000000725 suspension Substances 0.000 description 3
DZAUWHJDUNRCTF-UHFFFAOYSA-N 3-(3,4-dihydroxyphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(O)C(O)=C1 DZAUWHJDUNRCTF-UHFFFAOYSA-N 0.000 description 2
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
229920001800 Shellac Polymers 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000003276 anti-hypertensive effect Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000000576 coating method Methods 0.000 description 2
230000003111 delayed effect Effects 0.000 description 2
150000004683 dihydrates Chemical class 0.000 description 2
239000012055 enteric layer Substances 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
ZDYUUBIMAGBMPY-UHFFFAOYSA-N oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O ZDYUUBIMAGBMPY-UHFFFAOYSA-N 0.000 description 2
239000008024 pharmaceutical diluent Substances 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000004208 shellac Substances 0.000 description 2
229940113147 shellac Drugs 0.000 description 2
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 2
235000013874 shellac Nutrition 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
NLRUDGHSXOEXCE-PPHPATTJSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;hydrochloride Chemical compound Cl.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 NLRUDGHSXOEXCE-PPHPATTJSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
235000017060 Arachis glabrata Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
235000010777 Arachis hypogaea Nutrition 0.000 description 1
235000018262 Arachis monticola Nutrition 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
AKWHTKRUNUYXDS-UHFFFAOYSA-N Dihydroxyphenylpropionic acid Chemical compound OC(=O)CC(O)C1=CC=C(O)C=C1 AKWHTKRUNUYXDS-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
229940081735 acetylcellulose Drugs 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229940072056 alginate Drugs 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000003708 ampul Substances 0.000 description 1
210000000436 anus Anatomy 0.000 description 1
210000000702 aorta abdominal Anatomy 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
NWCHELUCVWSRRS-UHFFFAOYSA-N atrolactic acid Chemical compound OC(=O)C(O)(C)C1=CC=CC=C1 NWCHELUCVWSRRS-UHFFFAOYSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 1
238000013329 compounding Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
210000001198 duodenum Anatomy 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
210000003195 fascia Anatomy 0.000 description 1
239000012054 flavored emulsion Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
IYUKFAFDFHZKPI-DFWYDOINSA-N methyl (2s)-2-aminopropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@H](C)N IYUKFAFDFHZKPI-DFWYDOINSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
229920001206 natural gum Polymers 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
210000002254 renal artery Anatomy 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Epidemiology (AREA)
Emergency Medicine (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA258,527A 1975-08-13 1976-08-05 Compositions and method of treating hypertension Expired CA1069825A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/604,292 US4016288A (en)	1975-08-13	1975-08-13	Compositions and method of treating hypertension

Publications (1)

Publication Number	Publication Date
CA1069825A true CA1069825A (en)	1980-01-15

Family

ID=24419029

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA258,527A Expired CA1069825A (en)	1975-08-13	1976-08-05	Compositions and method of treating hypertension

Country Status (10)

Country	Link
US (1)	US4016288A (ja)
JP (1)	JPS5225035A (ja)
AU (1)	AU508424B2 (ja)
BE (1)	BE845117A (ja)
CA (1)	CA1069825A (ja)
DE (1)	DE2636328A1 (ja)
FR (1)	FR2320738A1 (ja)
GB (1)	GB1505959A (ja)
NL (1)	NL7608381A (ja)
ZA (1)	ZA764852B (ja)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4670578A (en) *	1983-08-29	1987-06-02	Merck & Co., Inc.	Process for crystalline salts of L or (S)-3-(3,4-dihydroxyphenyl)-2-methylalanine esters
US20050136103A1 (en) *	2003-09-17	2005-06-23	Ben-Sasson Shmuel A.	Compositions capable of facilitating penetration across a biological barrier
DK3209302T3 (da) *	2014-10-21	2019-05-13	Abbvie Inc	Carbidopa og l-dopa prodrugs og deres anvendelse til behandling af parkinsons sygdom
CN111588833A (zh) *	2020-07-09	2020-08-28	北京大元藏宝堂健康管理有限公司	一种调节高血压的产品

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3830827A (en) *	1970-03-23	1974-08-20	Merck & Co Inc	L-alpha-hydrazino-alpha-substituted-beta-(3,4-dihydroxyphenyl)propionic acid substantially free of the d isomer,the lower alkyl esters thereof,and the pharmaceutically acceptable salts thereof,wherein the substituent is lower alkyl
US3839585A (en) *	1970-08-05	1974-10-01	Merck & Co Inc	Method of treating hypertension
AU464903B2 (en) *	1970-11-12	1975-09-11	Merck & Co., Inc	Treatment of hypertension
US3795739A (en) *	1972-02-14	1974-03-05	Hoffmann La Roche	Treatment of parkinson disease
US3784703A (en) *	1972-02-29	1974-01-08	Merck & Co Inc	Method of treating hypertension

1975
- 1975-08-13 US US05/604,292 patent/US4016288A/en not_active Expired - Lifetime
1976
- 1976-07-28 NL NL7608381A patent/NL7608381A/xx not_active Application Discontinuation
- 1976-08-04 AU AU16558/76A patent/AU508424B2/en not_active Expired
- 1976-08-05 CA CA258,527A patent/CA1069825A/en not_active Expired
- 1976-08-09 GB GB33089/76A patent/GB1505959A/en not_active Expired
- 1976-08-11 FR FR7624515A patent/FR2320738A1/fr active Granted
- 1976-08-12 ZA ZA00764852A patent/ZA764852B/xx unknown
- 1976-08-12 BE BE169750A patent/BE845117A/xx not_active IP Right Cessation
- 1976-08-12 DE DE19762636328 patent/DE2636328A1/de not_active Withdrawn
- 1976-08-13 JP JP51096184A patent/JPS5225035A/ja active Pending

Also Published As

Publication number	Publication date
AU1655876A (en)	1978-02-09
US4016288A (en)	1977-04-05
GB1505959A (en)	1978-04-05
BE845117A (fr)	1977-02-14
FR2320738B1 (ja)	1979-05-18
NL7608381A (nl)	1977-02-15
DE2636328A1 (de)	1977-02-24
FR2320738A1 (fr)	1977-03-11
AU508424B2 (en)	1980-03-20
ZA764852B (en)	1978-03-29
JPS5225035A (en)	1977-02-24

Legal Events

Date	Code	Title	Description
1997-01-15	MKEX	Expiry

Publication	Publication Date	Title
US5942503A (en)	1999-08-24	Use of Epinastine for the treatment of pain
US4742054A (en)	1988-05-03	Treatment of mammals suffering from damage to the central nervous system
JPH06122668A (ja)	1994-05-06	トラマドールｎ−オキシド材料、そのエナンチオマー及び組成物、ならびにその利用
WO1986003489A1 (en)	1986-06-19	Pharmaceutically active derivatives of tryptophan and pharmaceutical compositions containing them
US4438138A (en)	1984-03-20	Reduction of cholesterol with meta-chloro α-t-butylaminopropiophenone
US4330558A (en)	1982-05-18	Pharmaceutical composition and method for treating peripheral orthostatic hypotension
US4256755A (en)	1981-03-17	Method of using N-substituted dihydro-2-oxazolamines as analgesics
EP0186241A1 (en)	1986-07-02	Hydrocodone/ibuprofen pharmaceutical compositions and method
GB2170707A (en)	1986-08-13	An immuno-regulator
CA1069825A (en)	1980-01-15	Compositions and method of treating hypertension
JPH08503710A (ja)	1996-04-23	ヒドロキシカルバゾール化合物の抗酸化心臓保護的使用およびそれを使用する治療方法
US3843796A (en)	1974-10-22	Antihypertensive agents
CA1295251C (en)	1992-02-04	Propiophenone derivatives for treatment of pollakiuria (frequency urination)
US4076834A (en)	1978-02-28	Therapeutic agents for improving cardiovascular function
US3839585A (en)	1974-10-01	Method of treating hypertension
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